(E)-3-methyl-2-phenylpent-2-enoic acid

Base Information

• Chemical Name: (E)-3-methyl-2-phenylpent-2-enoic acid
• CAS No.: 10457-70-2
• Molecular Formula: C₁₂H₁₄O₂
• Molecular Weight: 190.242
• NSC Number: 165629
• DSSTox Substance ID: DTXSID20419352
• Wikidata: Q82230327
• Mol file: 10457-70-2.mol

Synonyms:NSC165629;10457-70-2;DTXSID20419352;NSC-165629

Chemical Property of (E)-3-methyl-2-phenylpent-2-enoic acid

Chemical Property:

• Vapor Pressure: 0.000647mmHg at 25°C
• Boiling Point: 296.4°Cat760mmHg
• Flash Point: 202.1°C
• Density: 1.07g/cm³
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 190.099379685
• Heavy Atom Count: 14
• Complexity: 235

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(=C(C1=CC=CC=C1)C(=O)O)C
• Isomeric SMILES: CC/C(=C(\C1=CC=CC=C1)/C(=O)O)/C

Technology Process of (E)-3-methyl-2-phenylpent-2-enoic acid

There total 8 articles about (E)-3-methyl-2-phenylpent-2-enoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 69.0%

carbon dioxide (124-38-9,18923-20-1) + 1-phenyl-1-butyne (622-76-4,83585-27-7) + methylmagnesium bromide (75-16-1) → (2Z,4E)-3-ethyl-5-methyl-2,4-diphenylhepta-2,4-dienoic acid + (E)-2-phenyl-3-methyl-2-pentenoic acid (111795-28-9,10457-70-2)

Guidance literature:

1-phenyl-1-butyne; methylmagnesium bromide; With nickel(II) bromide diethylene glycol dimethyl ether; triphenylphosphine; In tetrahydrofuran; 2-methyltetrahydrofuran; at 60 ℃; for 1h; Schlenk technique; Inert atmosphere;

carbon dioxide; In tetrahydrofuran; 2-methyltetrahydrofuran; at 25 ℃; for 0.5h; regioselective reaction; Schlenk technique;

DOI:10.1002/ejoc.201801364

Reference yield: 69.0%

→ (E)-2-phenyl-3-methyl-2-pentenoic acid (111795-28-9,10457-70-2)

Guidance literature:

With nickel(II) bromide 2-methoxyethyl ether complex; triphenylphosphine; In tetrahydrofuran; at 60 ℃; for 1h;

In tetrahydrofuran; at 25 ℃; for 0.5h;

Reference yield:

1-Phenylprop-1-yne (673-32-5) + carbon dioxide (124-38-9,18923-20-1) + diethylzinc (557-20-0) → α-methylcinnamic acid (1199-77-5) + 3-methyl-2-phenylpent-2-enoic acid (10457-70-2) + (2E)-2-methyl-3-phenylpent-2-enoic acid

Guidance literature:

carbon dioxide; With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 0 ℃; for 0.25h; under 760.051 Torr; Inert atmosphere;

1-Phenylprop-1-yne; diethylzinc; In tetrahydrofuran; hexane; at 0 - 20 ℃; stereoselective reaction; Inert atmosphere;

DOI:10.1002/hlca.201600079

upstream raw materials:

3-hydroxy-3-methyl-2-phenyl-valeric acid

carbon dioxide

1-phenyl-1-butyne

methylmagnesium bromide